FIELD OF THE INVENTION
This invention is directed to new organic compounds and is particularly concerned with novel 1-substituted-6-phenyl-4H-s-triazolo [4,3-a][1,4]benzodiazepines of the formula 11 and a process for the production thereof.
The novel compounds and the process of production therefor can be illustratively represented as follows: ##STR4## wherein R is cyclopropyl, cyclopropylmethyl, or allyl; wherein R', R", and R.sub.1 are hydrogen or alkyl of 1 or 3 carbon atoms inclusive; and wherein R.sub.2, R.sub.3, and R.sub.4 are hydrogen, alkyl as defined above, fluoro, chloro, bromo, nitro, trifluoromethyl, or alkylthio.
The invention also comprises the pharmacologically acceptable acid addition salts of the compounds of formula 11.
The more desirable compounds are of the formula 11A: ##STR5## wherein R is cyclopropyl, cyclopropylmethyl, or allyl; R''' and R"" are hydrogen or methyl; R'.sub.2 is hydrogen, chloro, or fluoro; R'.sub.3 is hydrogen, or fluoro if R'.sub.2 is fluoro; R'.sub.4 is hydrogen, fluoro, chloro, bromo, nitro, or trifluoromethyl, and the pharmacologically acceptable salts thereof.
The most desirable compounds of this invention are of the formula 11B: ##STR6## wherein R is cyclopropyl, cyclopropylmethyl or allyl; wherein R'''is hydrogen or methyl; wherein R".sub.2 and R".sub.4 are hydrogen or chloro and the pharmacologically acceptable acid addition salts thereof.
The process of this invention comprises: treating a compound of formula 1 above, in an inert organic solvent at 10.degree.to 100.degree. C. with a secondary amine of the formula ##STR7## defined as hereinabove. An alkali metal iodide can be used to facilitate the reaction.